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16.12.4.1.4.7.5 Substitution of Halogens by Sulfonamides

DOI: 10.1055/sos-SD-116-00063

von Angerer, S.Science of Synthesis Knowledge Updates, (20111416.

Although benzenesulfonamides possess only low nucleophilicity, they are capable of replacing halogens in halopyrimidines after conversion into alkali metal salts to give the corresponding substitution products.[‌53‌,‌1105‌] A typical example is the reaction of 4,6-dichloropyrimidine with 4-tert-butylbenzenesulfonamide in the presence of sodium hydride, giving 4-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamide (683) in 61% yield (Scheme 384).[‌1106‌] An alternative is the use of copper(I) iodide as the catalyst, trans-cyclohexane-1,2-diamine as ligand, and potassium carbonate as base. Under these conditions 5-bromopyrimidine reacts with 4-tolu­enesulfonamide to give N-(pyrimidin-5-yl)-4-toluenesulfonamide in 60% yield.[‌1107‌]

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